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From $527 per night (USD)
VRBO
Charming colonial gem with multiple decks, gas grill, patio, and central AC
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Chatham Charmer Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $527 per night (USD)
VRBO
From $912 per night (USD)
Expedia
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
1.2 acres of beautiful waterfront property. Pond is great for canoes, fishing, and swimming. Canoe provided for tenant u ...
From $912 per night (USD)
Expedia
From $1102 per night (USD)
VRBO
FIVE BEDROOM-- WATERFRONT RETREAT ON RYDERS COVE, PERFECT SPOT TO KAYAK AND CANOE.
Bedrooms:
5
Bathrooms:
5
Sleeps:
13
Enjoy this Special Waterfront Retreat on Ryders Cove, a Perfect Spot to Kayak or Canoe! This 5 bedroom, 3.5 bath home ...
From $1102 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Renovated cottage 1 mile to beach in Chatham!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Totally renovated bungalow style cottage with a sunny open floor plan, brand new appliances and furnishings on quiet str ...
From $287 per night (USD)
Expedia
From $702 per night (USD)
VRBO
FOUR BEDROOM IN TOWN LOCATION -- CLOSE TO OYSTER POND BEACH AREA.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Chatham Bookends (main house) and Pencil Me Inn (guest cottage) tucked away just steps from Chatham Village. ...
From $702 per night (USD)
VRBO
From $498 per night (USD)
Expedia
Chatham Beach Cottage + loft Walk to the Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax with the whole family at this year round Charming Chatham Seaside Cottage , with just a short 5 minute walk to a b ...
From $498 per night (USD)
Expedia
From $1269 per night (USD)
VRBO
Royal Retreat: 935-C Renovated Luxury Chatham Home with Pool & Hot Tub
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
This property is professionally managed by Pretty Picky Properties Renovated Luxury Chatham Home with Pool & Hot Tub Ho ...
From $1269 per night (USD)
VRBO
$Centrally located home with patio, a\/c included, walking distance from town.$
From $656 per night (USD)
Expedia
Centrally located home with patio, a\/c included, walking distance from town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Centrally located vacation home with central air conditioning in an ideal location with 3 bedrooms, 2 full baths plus ...
From $656 per night (USD)
Expedia
From $968 per night (USD)
VRBO
FIVE BEDROOM -- AMAZING WATER VIEWS OF NANTUCKET SOUND, MINUTES TO ASSOCIATION BEACH
Bedrooms:
5
Bathrooms:
5
Sleeps:
11
Just 1/10 of a Mile to Deeded Association Beach with amazing water views of Nantucket Sound. You will never want to lea ...
From $968 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Wrap-Around Porch Mins. to Beach!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: 16643 - Tidal Treasure: Wrap-Around Porch Mins. to Beach! The Space: There isn’t a much more beautiful place t ...
From $362 per night (USD)
Expedia
From $1535 per night (USD)
VRBO
Luxurious Waterfront Home!
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
Summary: 15526 - Nautical Dream: Luxurious Waterfront Home! The Space: Orleans, Cape Cod is a picturesque town full of ...
From $1535 per night (USD)
VRBO
From $486 per night (USD)
Expedia
Three Bedroom Updated Home -- Just Minutes to Pleasant Bay, Town and Bike Path!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sun Filled, Completely Renovated 3 Bedroom, 2 Bath. Minutes from Pleasant Bay or Downtown, Perfect for your Cape Adven ...
From $486 per night (USD)
Expedia
From $824 per night (USD)
VRBO
Charming 3 bedroom 2.5 bath sleeps 6 - Walk to Town & Oyster Pond
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
A charming 3 bedroom, 2.5 bath cape with large kitchen and private backyard, patio and deck that abuts conservation lan ...
From $824 per night (USD)
VRBO
From $386 per night (USD)
Expedia
New construction home on quiet, private waterview lot near Pleasant Bay
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
We will provide an additional $250 discount for singles or couples -- please send a message and we'll discuss how to imp ...
From $386 per night (USD)
Expedia
From $489 per night (USD)
VRBO
The Boarding House, King bed comfort. Close to Nantucket Sound beaches.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This completely renovated 4 bedroom cape is less than 3 miles from Nantucket Sound beaches. Inside there is central air ...
From $489 per night (USD)
VRBO
From $383 per night (USD)
Expedia
Chatham Home ~ 1 Mi to Town & Oyster Pond Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Recently built and only 1 mile from Oyster Pond Beach, this Chatham vacation rental has everything you need for your nex ...
From $383 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
On over two acres of Oceanfront, 'Bayberry and Seadaisy Cottages at Ridgevale Beach face the temperate waters of Nantuc ...
From $396 per night (USD)
VRBO
From $1324 per night (USD)
Expedia
New Waterfront Townhome
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster. Beautifully and meticulously designed, this Town ...
From $1324 per night (USD)
Expedia
From $1030 per night (USD)
VRBO
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Ocean Harbor Waterfront. Stunning downtown Chatham Waterfront location with panoramic views, (Little Mill Pond) with ...
From $1030 per night (USD)
VRBO
From $431 per night (USD)
Expedia
5BR-Beautiful Chatham-Year Round-Sleeps up to ten (10) & 1 Mile to Town!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
My family and i live full time in lexington, ma. We decided to purchase a vacation home in chatham, ma because of the sh ...
From $431 per night (USD)
Expedia
$Walk to Beach-Water views-Central A\/C and WiFi$
From $743 per night (USD)
VRBO
Walk to Beach-Water views-Central A\/C and WiFi
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
3 Bedroom- 2 Bathroom- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $743 per night (USD)
VRBO
From $381 per night (USD)
Expedia
Pleasant Chatham Cape
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Pleasant Chatham Cape - A Classic Cape Cod Getaway with Modern Comforts Welcome to Pleasant Chatham Cape, a charming 4 ...
From $381 per night (USD)
Expedia
From $1594 per night (USD)
VRBO
Fabulous Family Capehouse, with Views, Beach and Dock! OPEN SUN Aug 17-Aug 24!
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
AVAILABLE SUN 8/10 to SUN 8/17, 2025! This sprawling family beach home is perfectly located on a hilltop with 3.5 acre ...
From $1594 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Solitude near the beach, High speed wifi
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Comfort, convenience and beauty a mere 5 minute stroll away from Ridgevale beach. Nestled in a quiet neighborhood, our b ...
From $361 per night (USD)
Expedia
From $801 per night (USD)
VRBO
Spacious Home on the Loop in Chatham
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Located on the Loop in scenic Chatham, this house rents Sunday to Sunday. The large living room opens onto a deck with ...
From $801 per night (USD)
VRBO
$~ 4 Mi to Dtwn: Chatham Home w\/ Fire Pit$
From $369 per night (USD)
Expedia
~ 4 Mi to Dtwn: Chatham Home w\/ Fire Pit
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
1,802 Sq Ft | Furnished Deck w/ Gas Grill | Fireplace | 13 Mi to Whydah Pirate Museum Welcome to the good life! Whether ...
From $369 per night (USD)
Expedia
From $2052 per night (USD)
VRBO
Location! Pool & Spa! 2 Primary Suites, Walk to Town, Beach, Chatham Bars Inn
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
**As is customary with Cape rentals, there is a cleaning fee and a 14.45% local and state lodging tax. Please enter desi ...
From $2052 per night (USD)
VRBO
From $1151 per night (USD)
Expedia
Luxury 4 Bedroom Harwich Home - Centrally Located
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Our home is located close to East Harwich shopping centers, restaurants, and Pleasant Bay for boating, fishing, and swim ...
From $1151 per night (USD)
Expedia
From $326 per night (USD)
VRBO
Serene home with WiFi, deck, & outdoor fireplace - walk to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Harwich Tranquility Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $326 per night (USD)
VRBO
From $1733 per night (USD)
Expedia
The Port: 177-CF Chatham Landmark Estate, Large Guest House, Heated Pool
Bedrooms:
8
Bathrooms:
8
Sleeps:
18
This property is professionally managed by Pretty Picky Properties Chatham Landmark Estate, Awesome Barn/Guest House, P ...
From $1733 per night (USD)
Expedia
From $454 per night (USD)
VRBO
Large Yard, Quiet; 300 Yd on Sidewalk to Hardings Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
If you have small children or would just like some peace and serenity, Blue Skye is for you. Lots of lawn to run and pl ...
From $454 per night (USD)
VRBO
From $705 per night (USD)
Expedia
Full Renovation! Amazing Spot with Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: 16620 - A Step Above: Full Renovation! Amazing Spot with Views! The Space: Our completely renovated and newly ...
From $705 per night (USD)
Expedia
From $115 per night (USD)
VRBO
Pleasant Forest Shores #1 S. Chatham: Classic Swedish ''Stuga'' style near beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
NOTE: Booking of EXISTING customers should begin on 02/01/25. New guests can ONLY apply for 2025 WAIT LIST at this time ...
From $115 per night (USD)
VRBO
From $1543 per night (USD)
VRBO
Historic Home With Private Beach On Stage Harbor
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
** Weekly rentals only: Saturday to Saturday ** ** No Pets or Parties** Our family has enjoyed this community for ov ...
From $1543 per night (USD)
VRBO
From $695 per night (USD)
VRBO
Spacious home in quiet neighborhood!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Spacious three bedroom, two and half bath home in Riverbay offers plenty of living space on a 1/2 acre wooded corner lot ...
From $695 per night (USD)
VRBO
$Beautiful Home w\/ Artistic Flair!$
From $402 per night (USD)
Expedia
Beautiful Home w\/ Artistic Flair!
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Summary: 16657 - Artist's Haven: Beautiful Home w/ Artistic Flair! The Space: On the Cul-de-sac of a private Chatham ne ...
From $402 per night (USD)
Expedia
$Centrally Located Home w\/ Patio Fire Pit!$
From $895 per night (USD)
VRBO
Centrally Located Home w\/ Patio Fire Pit!
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Summary: 16658 - Home Base: Centrally Located Home w/ Patio Fire Pit! The Space: Conveniently situated in the middle of ...
From $895 per night (USD)
VRBO
Click For Pricing
Expedia
North Chatham, Quaint Cottage, Great Yard, Welcome to Bobs Place
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
2 Bedroom - 1 Bathroom - Sleeps 4 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
Click For Pricing
Expedia
From $1151 per night (USD)
VRBO
Bungalow style home in downtown Chatham!
Bedrooms:
3
Bathrooms:
6
Sleeps:
11
Spend your Cape Cod vacation in our large, bungalow-style home, perfectly situated in the heart of downtown Chatham. We' ...
From $1151 per night (USD)
VRBO
From $304 per night (USD)
Expedia
Quaint 2 Bedroom Cottage Overlooking White Pond
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Must bring your own linens. Perfect getaway to relax and unwind. Located in a small 5 acre enclave of cottages nestled u ...
From $304 per night (USD)
Expedia
From $1183 per night (USD)
VRBO
Location and Luxury
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
LOCATION: The cottage is located in Chatham's old village, just a block from the ocean. The closest beach is Andrew Har ...
From $1183 per night (USD)
VRBO
From $1259 per night (USD)
Expedia
Family friendly luxury home with heated pool and spa
Bedrooms:
5
Bathrooms:
4
Sleeps:
14
Gorgeous home in Chatham with a brand new heated saltwater pool and hot tub. The open floor plan, combined living and ...
From $1259 per night (USD)
Expedia
From $281 per night (USD)
VRBO
Cozy one bedroom on White pond (Must bring your own linens)
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
2 Person only. Charming little classic Cape cottage located close to town, beaches and bike trail. The cottage is nestl ...
From $281 per night (USD)
VRBO
From $788 per night (USD)
Expedia
Refreshed Interior Central AC WIFI Large Yard Deck Great Chatham Location
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
4 Bedroom - 2 Baths - Sleeps 10 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Many ...
From $788 per night (USD)
Expedia
From $402 per night (USD)
VRBO
Classic home with deck, patio & yard - walk to Cockle Cove & Forest Beaches
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
South Chatham Sunshine Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $402 per night (USD)
VRBO
From $1001 per night (USD)
Expedia
Reuben Young House: Two 1st Floor King Master Suites. Close to Town & Beaches.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Charming circa 1820 antique newly renovated. close to downtown Chatham (1.5 miles). Close to Fish Pier, Ryders Cove, Oys ...
From $1001 per night (USD)
Expedia
From $515 per night (USD)
VRBO
Chatham walk to Cape Cod beach
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
A Very Short Walk to Hardings Beach. Ocean-side private neighborhood. Chosen by Condé Nast Traveler as “One of the Bes ...
From $515 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Charming Downtown Chatham
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Charming in town apartment above retail shops overlooks the Main St. Walk to beaches, nearby shops & restaurants, band c ...
From $315 per night (USD)
Expedia
$Chatham 3 Bedroom\/2 Bath Retreat$
From $477 per night (USD)
VRBO
Chatham 3 Bedroom\/2 Bath Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully renovated and spacious 3 Bedroom 2 Full Bath Home on a private 1/2 acre setting in one of Chatham's sought a ...
From $477 per night (USD)
VRBO
$Lovely Stage Harbor Estate Guest House W\/Private Beach to Use$
From $401 per night (USD)
Expedia
Lovely Stage Harbor Estate Guest House W\/Private Beach to Use
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Lovely guest house on quiet and picturesque Stage Harbor! Right on town way with 30 second walk to the water and use of ...
From $401 per night (USD)
Expedia
From $858 per night (USD)
VRBO
Near beach and town, private, AC, pet friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
3 Bedrooms- 3 Bathrooms- Sleeps 8 A 7-night Friday-to-Friday rental reservation is required during peak summer weeks. Ma ...
From $858 per night (USD)
VRBO
$\Chatham Up\ - Come Stay, Relax, Have Fun!$
From $327 per night (USD)
VRBO
\"Chatham Up\" - Come Stay, Relax, Have Fun!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
"CHATHAM UP" is a wonderful home located in North Chatham within a very established family neighborhood which is great f ...
From $327 per night (USD)
VRBO
From $548 per night (USD)
VRBO
Stunning 3BR Home - Close to Town & Beaches (2159)
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Nestled in East Harwich, this beautiful 3BR/3BA Harwich home features a welcoming open floor plan with high ceilings, ha ...
From $548 per night (USD)
VRBO
From $558 per night (USD)
Expedia
Excellent Chatham Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This Chatham beauty is a Newly built cottage which is walking distance to Pleasant Bay and a short drive to town. A per ...
From $558 per night (USD)
Expedia
From $1210 per night (USD)
VRBO
CHARMING COASTAL COTTAGE IN NORTH CHATHAM
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
...
From $1210 per night (USD)
VRBO
From $524 per night (USD)
Expedia
Charming two year old 3Bd Rm 4 bath home .6mi to Ridgevale Beach
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Newly built home, app 2900 sq feet, The 1st floor includes a master bedroom with private bath with tub/shower, king siz ...
From $524 per night (USD)
Expedia
From $465 per night (USD)
VRBO
Chatham Break! 3BR, large quiet yard, walk to shops + restaurants.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Traditional Cape Cod style home with a large, private yard, sunny deck, outdoor shower and hammock in a quiet Chatham ne ...
From $465 per night (USD)
VRBO
From $910 per night (USD)
Expedia
New Waterfront Townhome
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
This picture perfect Townhome is set on 17.5 acres on beautiful Oyster Pond in the heart of Chatham, Cape Cod, Massachus ...
From $910 per night (USD)
Expedia
From $784 per night (USD)
VRBO
WATER VIEW OF STETSON COVE! UPDATED HOME WITH SO MUCH TO OFFER!
Bedrooms:
1
Bathrooms:
1
Sleeps:
8
Sparkling Updated Home With Lovely Views Of Stetson Cove! This spacious, immaculate home boasts a large kitchen with d ...
From $784 per night (USD)
VRBO
From $878 per night (USD)
VRBO
Sweetest Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
This updated 4-bedroom 2-bathroom home has the best view on Pleasant Bay, hands down. The open floor plan is ideal for l ...
From $878 per night (USD)
VRBO
From $6793 per night (USD)
VRBO
Your Ultimate Vacation Destination!
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
This is your ultimate vacation destination! Simply stunning, custom built home with a grand farmer's porch! Sit and sip ...
From $6793 per night (USD)
VRBO
$CHATHAM WATER FRONT\/VIEW HOUSE FIRST TIME RENTAL$
From $780 per night (USD)
Expedia
CHATHAM WATER FRONT\/VIEW HOUSE FIRST TIME RENTAL
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Perfect vacation spot. Enjoy your vacation on this 3 bedroom 2 bath, Central air conditioned house bordering Emery Lake ...
From $780 per night (USD)
Expedia
From $484 per night (USD)
VRBO
Air Conditioned, King bed Comfort .Dog friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cranberry Cove, beautiful bright open-plan 3 bedroom house with central AC, a great room made for family time, with vaul ...
From $484 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Cozy Cottage close to Beaches, Boating, Biking, Shopping and more
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Centraly located on the elbow of Cape Cod, cozy little cottage in isolated neighborhood of like summer homes. Two bedroo ...
From $282 per night (USD)
Expedia
From $629 per night (USD)
VRBO
Secluded Chatham Cape Cod House Stage Harbor Area
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Very secluded 3br family friendly (pets considered) full Cape at the end of a cul-de-sac. Located in rural Stage Harbor ...
From $629 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Fabulous Quiet Cape, Close to Beach, Central Air, Perfect for Families
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy your quiet family get-away in a lovely, newer construction beautifully decorated cape with central air. Just a co ...
From $319 per night (USD)
VRBO
From $518 per night (USD)
VRBO
Cozy Cape near Chatham Center
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
You will be sure to enjoy your time in the idyllic town of Chatham, MA in Cape Cod. Our home is 1/2 mile from the qua ...
From $518 per night (USD)
VRBO
From $480 per night (USD)
Expedia
Lovely Cape Cottage Home < 1 mile to the beach! Gigabit WIFI 1000Mbps
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Relax at this charming South Chatham coastal retreat! Situated just 0.8 miles to Forest Beach & close proximity to the C ...
From $480 per night (USD)
Expedia
From $760 per night (USD)
VRBO
Beautiful Chatham
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This property is located in the Ryder's Cove area of Chatham MA. The main house consist of 2 bedrooms on the upper leve ...
From $760 per night (USD)
VRBO
From $509 per night (USD)
Expedia
Harwich Cape Escape: Minutes from Everything!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Harwich Cape Escape: 4 Bedrooms, 2.5 Baths, Sleeps 8 This beautiful two-story 4BR/2.5 BA Cape Cod home features almost ...
From $509 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Close to Hardings Beach & Private Access to Oyster River
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Comfy and cozy four bedroom home near Hardings Beach! This recently updated Cape cottage is filled with new furnishings, ...
From $424 per night (USD)
VRBO
From $626 per night (USD)
Expedia
Stylishly Furnished Home- Access to Pleasant Street Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
*Cancellation policy at end of property description.* Sophisticatedly furnished and well maintained 3BR/2BA with a bon ...
From $626 per night (USD)
Expedia
From $660 per night (USD)
VRBO
Fantastic Rooftop Deck * 3 Min Walk to Ocean Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
In a Few Words Walk to the beach from this classic New England cottage. Head to the rooftop deck for coffee or cocktai ...
From $660 per night (USD)
VRBO
From $1113 per night (USD)
Expedia
Family Friendly Home with Private Bog View-Close to 2 beaches & town center.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Newly remodeled in 2020, this designer 4 BR, 3 full bath house sleeps 10 (8 preferred) and has everything you need to ma ...
From $1113 per night (USD)
Expedia
From $1268 per night (USD)
VRBO
Pet friendly! Beautiful decor and great outdoor entertaining space for the whole family.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy your Chatham vacation at this spacious, newly furnished, 4 bedroom, 3 bath home. Offering 1 king, 2 queens, a bunk ...
From $1268 per night (USD)
VRBO
From $1519 per night (USD)
Expedia
Spend your quintessential Cape Cod vacation, in a beautifully renovated 1862 Farm House on Stage Harbor Road!
Bedrooms:
6
Bathrooms:
6
Sleeps:
13
Experience your quintessential Cape Cod vacation in a beautifully renovated 1862 Farm House on Stage Harbor Road! Lush g ...
From $1519 per night (USD)
Expedia
From $541 per night (USD)
VRBO
Cozy Cape Cod Retreat, Just One Block to Hardings Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cozy saltbox located only a couple of blocks from Chatham's popular Harding's Beach! Relax and enjoy your Chatham vacati ...
From $541 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Amazing Location! Lakefront Waterside Deck
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: 16629 - Dock Holiday: Amazing Location! Lakefront Waterside Deck The Space: Get ready for a week of rafting, c ...
From $669 per night (USD)
Expedia
From $598 per night (USD)
VRBO
Walk to Chatham Center or bike the Cape Cod Rail Trail!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Wonderful summer rental, filled with new furnishings and centrally located in Chatham! The Cape Cod Rail Trail is right ...
From $598 per night (USD)
VRBO
From $386 per night (USD)
Expedia
Kid-Friendly Ridgevale Beach is an easy stroll from this comfy beach house!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
.... PET FRIENDLY! ... Recently updated, this classic summer beach cottage is a quick walk to popular Ridgevale Beach! A ...
From $386 per night (USD)
Expedia
From $522 per night (USD)
VRBO
Luxury Chatham Town Home. Close to town & beaches!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sunlight filled luxury town home overlooking a beautiful pond, with three floors of living space. Located less than a mi ...
From $522 per night (USD)
VRBO
From $463 per night (USD)
Expedia
Bright Charming South Harwich Home, Private Backyard, Close to Beaches & Shops
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful single family home in South Harwich, conveniently located right off of Rt. 28. Only 500 feet from the Cape Cod ...
From $463 per night (USD)
Expedia
From $421 per night (USD)
VRBO
15 Minute Walk to Forest Beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: 16632 - Casa Al Mare: 15 Minute Walk to Forest Beach! The Space: Your perfect seaside getaway starts with this ...
From $421 per night (USD)
VRBO
$🐶 Dog Friendly Fenced in Yard! 3\/2 🏠 1.1 mi to 🏝 WIFI - perfect fall rental!$
Click For Pricing
Expedia
🐶 Dog Friendly Fenced in Yard! 3\/2 🏠 1.1 mi to 🏝 WIFI - perfect fall rental!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Modern 3 bedroom, 2 full bath ranch style home located in Chatham! 1/10th of a mile to Old Colony Bike path and 1.1 mile ...
Click For Pricing
Expedia
From $666 per night (USD)
VRBO
Perfectly located, with central AC. 3BR, sleeps 6-8
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Our house has undergone a complete renovation with all new updates. The house has a complete master suite on the first ...
From $666 per night (USD)
VRBO
$Quaint Chatham home w\/beautiful backyard & furnished multi-level deck, dogs OK$
From $494 per night (USD)
Expedia
Quaint Chatham home w\/beautiful backyard & furnished multi-level deck, dogs OK
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Lucky Number Seven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $494 per night (USD)
Expedia
From $369 per night (USD)
VRBO
WALK TO RESTAURANTS, SHOPS & LIQUOR STORE!! CLOSE TO DOWNTOWN CHATHAM!!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This adorable cottage is in an ideal location in West Chatham! Located on a quiet cul-de-sac with five other homes. A 5 ...
From $369 per night (USD)
VRBO
$Apres Sea - Chatham 4 Bedroom w\/ Central AC$
From $1252 per night (USD)
Expedia
Apres Sea - Chatham 4 Bedroom w\/ Central AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Ideal location just minutes to bike trail, beaches and downtown Chatham! This home is represented by Nauset Rental, a l ...
From $1252 per night (USD)
Expedia
From $1019 per night (USD)
VRBO
Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gorgeous panoramic views of Mill Pond and just a short walk to downtown Chatham! Experience beautiful water views with y ...
From $1019 per night (USD)
VRBO
$1 Mi to Beach: Home w\/ Fire Pit & BBQ in Cape Cod!$
From $616 per night (USD)
Expedia
1 Mi to Beach: Home w\/ Fire Pit & BBQ in Cape Cod!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
2,688 Sq Ft | Dog Friendly w/ Fee | Wet Bar | Expansive Yard Nestled in the heart of South Chatham, this 3-bed, 2.5-bat ...
From $616 per night (USD)
Expedia
From $635 per night (USD)
VRBO
Walk to town, playground and the beach!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This well-maintained and updated 4 bedroom, 2 bath home is an excellent choice for your Chatham vacation. With two quee ...
From $635 per night (USD)
VRBO
$Sleeps 10+\/Walk To Buck's Pond Lake! Close To Beach\/Golf\/Restaurants$
From $592 per night (USD)
Expedia
Sleeps 10+\/Walk To Buck's Pond Lake! Close To Beach\/Golf\/Restaurants
Bedrooms:
5
Bathrooms:
4
Sleeps:
12
You will never have to get in your car after arriving. Relax on the deck. Walk with the kids to Buck's Pond. We have ...
From $592 per night (USD)
Expedia
$Water View-Walk town\/beach, pets considered, Linen Option$
From $993 per night (USD)
VRBO
Water View-Walk town\/beach, pets considered, Linen Option
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
It's all about LOCATION-just steps from deeded access to the Mill Pond where you can launch your Kayak without ever havi ...
From $993 per night (USD)
VRBO
From $757 per night (USD)
Expedia
Charming Chatham Home Close to Bassing Harbor!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
*Cancellation policy at end of property description.* Looking for the perfect home for your next Chatham vacation? Thi ...
From $757 per night (USD)
Expedia
From $911 per night (USD)
VRBO
Water Views in Chatham!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*Cancellation policy at end of property description.* Charming, perfect location and every amenity you could want! Th ...
From $911 per night (USD)
VRBO
From $677 per night (USD)
Expedia
Located in the heart of downtown Chatham, this gem offers an easy walk to everything.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located in the heart of downtown Chatham, this gem offers an easy walk to dinner, ice cream, shopping, a movie, Oyster P ...
From $677 per night (USD)
Expedia
From $421 per night (USD)
VRBO
Waterfront on Private Lake!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Summary: 16644 - Lover's Lookout: Waterfront on Private Lake! The Space: Enjoy your best days of summer at our waterfro ...
From $421 per night (USD)
VRBO
From $1946 per night (USD)
Expedia
Booking for Summer 2025!
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Heated Pool and hot tub! Close to Chatham Bars Inn and downtown Chatham. Perfect location for a small or large family/fr ...
From $1946 per night (USD)
Expedia
From $1414 per night (USD)
VRBO
Main Street in Chatham!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Main Street in Chatham! Spend your summer vacation relaxing on the front porch of this charming, quintessential Cape Cod ...
From $1414 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Cape Cottage - 10 minute walk to Red River Beach
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Classic Cape House just minutes away from Red River Beach! 3 BDR, 1 BA, last house on quiet dead end street. Short wal ...
From $515 per night (USD)
Expedia

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Results: 669 Rentals